6-Phenylnicotinaldehyde → 2-Methyl-1-(6-phenylpyridin-3-yl)propan-1-ol

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Reaction Steps

Synthesized using compound 43b (283 mg, 1.55 mmol) and isopropylmagnesium chloride (1.55 mL, 3.10 mmol, 2 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (4:1) as eluent. Orange solid. Yield: 138 mg, 40%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.82-0.93 (m, 3H), 1.02 (d, J=6.6 Hz, 3H), 1.95-2.08 (m, 1H), 4.46 (d, J=6.6 Hz, 1H), 7.39-7.44 (m, 1H), 7.45-7.50 (m, 2H), 7.68-7.75 (m, 2H), 7.96-8.01 (m, 2H), 8.57 (d, J=1.9 Hz, H); MS (ESI): m/z=228.26 [M+H]+.

Provenance & Evidence